Hydrochloric Acid → HCID 90388282, compound

Participants

Reaction Steps

To a solution of compound 13 (145 mg containing the unseparated 4aR diastereomer, 0.54 mmol) in THF (10 mL) was slowly added lithium tri-t-butyloxyaluminohydride at −40° C. After 2 h, 6 N HCl was added at −40° C. and the reaction was warmed to room temperature for 30 min. The product was extracted into EtOAc (50 mL×2). The combined extracts were dried, filtered, and removed. The residue was purified by flash column chromatography (silica gel eluted with 25% EtOAc in hexanes) and the product from the 4aR diastereomer separated to afford pure compound 14 (82 mg, 56%): mp 175-177° C.; [α]D20 +34.5 (c 0.22, CHCl3); 1H NMR (CDCl3) δ 3.58-3.49 (m, 1H), 0.76 (s, 3H); 13C NMR (CDCl3) δ 221.1, 71.4, 47.9, 45.7, 40.1, 39.2, 38.8, 38.5, 36.2, 35.6, 35.5, 31.7, 29.6, 29.3, 28.4, 25.5, 24.1, 13.5; IR νmax 3398, 1736 cm−1. Anal. Calcd for (C18H28O2): C, 78.21; H, 10.21. Found: C, 78.12; H, 10.40.

Provenance & Evidence